Xanthone
Xanthone
Xanthone is an organic compound with molecular formula: C13H8O2.
The IUPAC name for xanthone is: 9H-Xanthen-9-one.
This organic compound is found naturally in several plants, especially those of the Gentiana, Hypericum and Swertia genus. It can be extracted from these plants and is used in various sectors, including pharmaceuticals and cosmetics, for its bioactive properties.
From a physical point of view it is a white solid.
Xanthone was introduced in 1939 as an insecticide and is currently used as an ovicidal for moth eggs and as a larvicide. Xanthone is also used in the preparation of xanthidrol, which is used in the determination of urea levels in the blood. It can also be used as a photocatalyst.
Xanthone can also be prepared through chemical synthesis, by heating phenyl salicylate:
in total six methods have been reported to synthesize xanthone derivatives:
The Michael-Kostanecki method uses an equimolar mixture of a polyphenol and an O-hydroxybenzoic acid, which are heated with a dehydrating agent.
The Friedel-Crafts method has a benzophenone intermediate.
The Robinson-Nishikawa method is a variant of the Hoesch synthesis but with low yields.
The Asahina-Tanase method synthesizes some methoxylated xanthones and xanthones with acid-sensitive substituents.
The Tanase method is used to synthesize polyhydroxyxanthones.
The Ullman method condenses a phenol with an O-chlorobenzene and cyclizes the resulting diphenyl ether.
Xanthone forms the core of a variety of natural products, such as mangosteen or lichexanthone. These compounds are sometimes referred to as xanthones or xanthonoids. Over 200 naturally occurring xanthones have been identified. Many are phytochemicals found in plants of the Bonnetiaceae, Clusiaceae and Podostemaceae families. They are also found in some species of the Iris genus. Some xanthones are found in the pericarp of the mangosteen fruit (Garcinia mangostana), as well as in the bark and wood of Mesua thwaitesii.
Warning: The information provided is not medical advice and may not be accurate. The contents are for illustrative purposes only and do not replace medical advice.